On the anniversary of the Bosman ruling, where have all the great freebies gone to challenge our top 10 transfers?

The big guns of the Barclays Premier League may be preparing to splash millions more of their cash this summer, and Manchester City have already spent nearly £100million to launch their fresh assault on the title, but 16 years ago today transfers in English football changed forever.

In 1997 English football chiefs agreed to adopt the Bosman ruling, the European law which allowed out-of-contract players aged 24 and over to move to other clubs for nothing.

The change came after Jean-Marc Bosman, a player for RFC Liege, challenged his club after they had refused to let him join French team Dunkerque without a transfer fee, even though he was out of contract. In the meantime his wages were reduced because he was no longer a first team player.

Bosman took his case to the European Court of Justice in Luxembourg, suing for restraint of trade. Five years after trying to negotiate his move to Dunkerque, Bosman finally won his case. But the former Belgian youth player’s career had stagnated and eventually he was to end up bankrupt and broken.

In December 1995, the court ruled that football’s transfer system placed a restriction on the free movement of workers and was prohibited by Article 39(1) of the EC Treaty.

The man who started it all: Jean-Marc Bosman made it possible for clubs to move for free

Their ruling meant that all EU players, including Bosman, were permitted free transfers at the end of their contracts. The Bosman ruling also ended the practice of UEFA imposing quotas on the number of foreign players in squads, which had an impact in particular on teams competing in Europe.

The decision in Luxembourg
revolutionised football. Players, and their agents in particular, became
far more powerful. The fees paid to agents for bringing free transfers
to clubs, plus the extra wages an out of contract player could command,
meant clubs were still paying substantial funds to get the best.

It also brought a change of mind-set from clubs who wanted to prevent players leaving on a Bosman transfer.

Back home: Teddy Sheringham returned for a second stint at Tottenham on a free from Manchester United

Freebees: Gianluca Vialli and David Beckham both moved on Bosnan's in their career

Life in Spain: Steve McManaman enjoyed sucess at Real Madrid

The first high profile English player to take advantage of the new rules was Liverpool’s Steve McManaman, a home-grown player, who left Anfield for nothing to join Real Madrid.

His transfer was a lesson to clubs and prompted them to offer massive wages to keep their players in contract, rather than risk losing them. The downside, as clubs are still discovering, is that relegation can be costly and players can still be on huge salaries which can cripple clubs out of the Premier League.

BEST BOSMAN SIGNINGS

Gianluca VialliJuventus to Chelsea 1996

Gary McAllisterCoventry City to Liverpool 2000

Sol CampbellTottenham to Arsenal 2001

Teddy SheringhamManchester United to Tottenham 2001Portsmouth to West Ham United 2004

Jay-Jay OkachaParis St Germain to Bolton Wanderers 2002

Esteban Cambiasso Real Madrid to Inter Milan 2004

Steve McManamanLiverpool to Real Madrid 1999

Michael Ballack Bayern Munich to Chelsea 2006

David BeckhamReal Madrid to LA Galaxy 2007

Mathieu Flamini Arsenal to AC Milan 2008

But clubs are still prepared to offer large salaries and incentives to keep their best stars. In December last year it was revealed Ashley Cole, Frank Lampard and Theo Walcott were all running down their contracts. All three signed new deals.

Manchester City meanwhile did not renew the contract of Kolo Toure, who turned up at Liverpool on a free transfer two months ago.

Newcastle on the other hand forked out a couple of million to ensure they beat the crowds to sign France international Moussa Sissoko from Toulouse.

The 23-year-old France international was letting his contract expire, and Newcastle, after watching the midfielder for several months, decided to pay a little extra in January to his French club rather than lose him to another interested party this summer.

While his name is still associated with one of the most important pieces of football legislation, and has made hundreds, if not thousands, of footballers very wealthy, Jean-Marc Bosman gained very little from the ruling.

He played just 12 more professional games in his career with Olympique Saint-Quentin and then blew the little money he made from the case in a series of bad business investments, even descending into alcoholism and depression while living on benefits.

Earlier this year Bosman, now 48, was sentenced to a year in prison following an assault on his then girlfriend and her daughter.